Calabria’s coastal watchtowers reflect the region’s cultural and architectural evolution. They were built during the Angevin period to assert control over Southern Italy, and gained strategic importance under Charles V, serving for observation and communication against Turkish invasions. Originally, 130 towers were documented, but only 70 remain, mostly in neglect. This study uses modern technologies to catalog, evaluate, and promote them. A digital map using QGIS has been developed, integrating data on conservation status, restorations, and building materials, while correlating them with environmental factors, local outcropping lithologies, landslides and coastal erosion. The study focuses on five towers: Saracena (Palmi, RC), Ruggero (Bagnara, RC), Cavallaro (Marina di Gioiosa Jonica, RC), La Rocchetta (Briatico, VV), and Marrana (Ricadi, VV). Preliminary observations identified building materials and degradation forms, including saline efflorescence, flos tectorii, alveolisation, and biological colonization. To analyze their minero-petrographic features, future analytical methods will include Polarized Optical Microscopy (POM), X-Ray Powder Diffraction (XRD), X-Ray Fluorescence Spectrometry (XRF), Scanning Electron Microscopy with Energy Dispersive Spectroscopy (SEM–EDS) and Ion Chromatography (IC). Additionally, drone-based photogrammetry will generate high-precision 3D models, assessing the impact of earthquakes, coastal erosion, and landslides on the watchtowers. Later stages of this research will integrate Heritage Building Information Modeling (H-BIM) with 3D GIS, for a multi-scale analysis, structural monitoring, and environmental risk assessment. Moreover, augmented reality will be used to enhance public engagement, making these towers more accessible to tourists, students, and researchers. This multidisciplinary approach combines tradition and innovation to preserve and promote Calabria’s coastal watchtowers, ensuring their safeguarding and sustainable valorization.